Alkyl-oxy-acetyl urea and process of making same.



UNITED STATES PATENT OFFICE.

neute- CLEMMENSEN AND ARNO MICHIGAN, AssIeNoRs TO LD H. (J. HEITMANN, OF DETROIT,

PARKE, DAVIS & COMPANY, OF DE- TROIT, MICHIGAN, A OORPORATIOI ALKYL- oxY-ACETifL UREA AND PROCESS QF MAKING SAME.

Application filedJlpril 1,

pounds which may be designated as ureids of alkyl-oxy-acetic acids; and the invention consists, first, in the new chemical compound, and, second, in the process of manufacturing the same.

The new body is a condensation. product of an alkyl-oxy-acetic acid and a urea and may be formed by the treating of the said substances with a condensing agent or by treating an ester of the alkyl-oxy-acetic acid and the urea with the condensing agent. It may also be formed by other methods, as hereinafter set forth. a

i In the formation of various specific compounds included in the class different sub stances may be employed, and we will thereforedescribe one specific case in which the di-ethyl-oxy-acetic acid is combined with urea to form the diethyl-oxy-acetyl urea.

The union of the ingredients may beproduced by several methods; but it is preferably accomplished in solution and preferably by the employment of alcohol as a solvent. The ingredients are dissolved in the alcohol in molecular proportions and are then treated with a condensing agent, preferably an alkalialeoholate, after which the mixture is heated on a steam-bath, preferably for several hours. During this period the reaction which begins immediately is completed and may be expressed as follows: aaeata iiiiiii iizoo +ao,n,,on.

In the above reaction two molecules of the di-ethyl-oXy-acetic ester combined with one molecule of the urea andone molecule of the condensing agent form a sodium salt of the desired product. The free substance may then be obtained by acidifying the solution With any suitable acid, such as hydrochloric, to produce the following reaction: o,,n, eoncome.romeo noi= The result of the complete reaction is there- Specifioation of Letters Patent.

1905.. Serial No. 253,255.

Patented Aug. 22, 1905.

fore the formation of one molecule of di*ethyloxy-acetyl urea and one molecule of a sodium salt of the acid used.

In the reaction above given the condensing agent-viz., sodium alco'holateenters into the desired product; but where other condensing agents are employedsuch, forinstance, as fuming sulfuric acid-the product may be formed Without a chemical change of the condensing agent. To obtain the pure product, thealcohol is removed by distillation, after which the sodium salt and free acid are removed by Washing with water. The yield is nearly theoretical.

Inplace of the specific ingredients above described any alkyl-oxy-acetic acid or its ester and any of the ureassuch as urea, acetylurea, alkyl-ureas, thio-urea, alkyl-thio-urea, urethancs and guanidin-may be combined by the use of any suitable condensing agent such as freshly-burned alkali earth oxids, metallic alkalies, fuming sulfuric acid, phosphorous chlorids, thionyl chlorid, sulfuryll chlorid, sulfonie-acid'chlorids, and other organic-acid chlorids as, for instance, acetyl chlorid, carbonyl chlorid, organic and inorganic acid anhydrids.

As a modification of the process above described, the compound may be formed by mix- .ing a urea with an alkyl-oxy-acetyl chlorid, whereupon reaction immediately takes place as follows:

mom,noonooowmmaoo:

' 0,11, ,oonc m1 ,oo+no1. The result of this reaction is the immediate formation of the free product.

In a further modification of the process the compound maybe formed bymixingone molecule of guanidin with two molecules of alkyloxy-acetic ester and one molecule of sodium alcoholate, as a result of which one molecule of alkyl-oXy-acetyl guanidin is obtained. To obtain the free alkyl-oxy-acetyl urea, this product may be oxidized by any suitable oxidizing agent---as, for instance, nitric acid in the presence of sulfuric, as indicated by the following reaction;

The product obtained may be broadly designated a ureid of alkyl-oxy-aeetic acid and is characterized by the following properties: It is a heavy, oily, colorless liquid, soluble in water, having a slight ethereal odor "above given, the following: it has a specific gravity of 1.1107 and boils at thirty-six millimeters pressure at a temperature of 186" centigrade, and is soluble in water in the proportion of one part of the substance to twenty parts of distilled water.

- The'action of the substance when given in I doses of about two grams causes a natural physiological sleep without producing any apparent disagreeable after ell'eets.

In the useof the term allcyl-oxy acetic acid in the claims we mean to include either the acid or its ester.

What we claim as our invention is- 1. The herein-described substance which is a condensation product of allgvl-oxy-acetic acid and'a urea and is characterized by its hypnotic action and the following physical properties: In its pure form, it is a colorless liquid, heavier than water, having a slight ethereal odor and an acid taste, issolnble in organic solvents, such as alcohol, other, chloroform,

aceto e, benzol, glycerin, may be distilled under reduced pressure and combines with basic substances to produce salts which also have hypnotic action.

2. The herein-described substance, which is a condensation product of di-ethyl-oxy-acetic acid and urea and is characterized by its h vpnotic action and the following physical properties; it is a colorless oily liquid, heavier than water, having a slightethereal odor and an acid taste, a specilic gravity of 1.1107 and boils at thirty six millimeters pressure at a temperature of 186 centigrade; it is soluble in water in proportion of about .one part of substance to twenty parts of distilled water, readily soluble in water containing alkali in solution, forming soluble crystalline salts; it is very soluble in organic solvents, such as alcohol, ether, chloroform, acetone, benzol, glycerin, and may be represented by the following formula:

3] The herein-described process of obtaining alkyl-oxy-acetvl ureas, which consists in treating a mixture of allzyl-oxy-acetic acid and a urea with a condensing agent.

4. The herein-described process 0% ublallling all yl-ox ,'-acet,\ l nreas, which consists in condensing an alkyl-oXy-acetic ester and a urea with an all;alialcoholate.

J. The herein-described process of forming di-ethyl-oXy-acetyl urea, which consists in treating di-ethyl-oXy-acetic csler and a urea in alcoholic solution with an alltali-alcohola'te as a condensing agent, in heating the mixture to facilitate reaction in then acidifying the solution and distilling off the alcohol, separating the oily productfrom the solution, washing with water and drying.

in witness whereof we have hereunto set our hands this 30th day of arch, 1WD.

\Vitnesses:

AMELIA \l'ltminis. .las. l. Baum. 

